Ash's Biggest Challenge
by Whiscash
Summary: Growing up, Ash always thought that his hardest challenges would always be in Pokemon leagues and battles. Now, as an adult, he realises that the biggest challenge he'll face is telling Misty just how much she means to him. (Pokeshipping, co-written with PineStarShip!)


**Ash's Biggest Challenge**

 **by Whiscash & PineStarShip**

 **pairing:** Pokeshipping (Ash x Misty)

 **notes:** my first co-write with the awesomely talented **PineStarShip**! :D So if you don't like this, take it up with him XD seriously though, this was so much fun to write and collaborate on so massive thanks to PineStarShip for the idea - if you haven't already, go check his fics out! I haven't written Pokemon in way too long, but how could I say no to some Pokeshipping fluff :P So please enjoy, and as always if you have any thoughts we would love to hear them~!

* * *

"ASH! Have you been listening to anything I've been saying?" Misty asked, annoyed at her partner's apparent lack of concentration at what she was saying.

"Sorry, Misty, I've got a lot on my mind right now" Ash replied quietly, avoiding eye contact with the angry redhead.

"Like what? You've been saying that for the past three months, ever since you got back from the Kalos region," Misty snapped at him.

"It doesn't matter. What were you saying?" Ash muttered, trying to get Misty to drop the subject of his time in the Kalos region.

"I was saying... What do you think of maybe visiting Brock in Pewter City?"

"Oh yeah, sounds like a great idea. I've not seen Brock for nearly a year or so now," Ash agreed.

"Great! I'll go call him right now."

As Misty ran off upstairs, Ash let out a sigh of frustration. It wasn't, despite what some people said, _that_ unusual for him to have a lot on his mind - he'd had a lot to think about since he returned from his trip back to the Kalos region. But this was even more important, he thought - this was _Misty_ , and he cared about her way more than winning any battle, even if it had taken him a while to figure it out. He knew he wanted to be with her forever, but...he didn't know how he was going to _say_ it. He couldn't just say whatever came into his head like he normally did - what if she thought it was some dumb joke? What if she _said no_?

"Pika." Ash snapped out of his reverie as Pikachu patted his leg, looking up at him with understanding eyes. As usual, his best friend seemed to know exactly what he was thinking.

"I know, buddy," he said, lifting the Pokemon up onto his lap and scratching him between the ears as he thought. He could ask Brock for advice, but for someone who claimed to be an expert on romance, Ash couldn't remember his moves ever working on any girl they'd met - well, except one. "I'm gonna ask her soon, I swear! But... _how_ am I gonna do it?"

"Do what?" Misty stuck her head out of the doorway seemingly out of nowhere, and Ash almost fell off his chair.

"Do...uhhh...the crossword puzzle!" he declared, flashing her what he hoped looked like an innocent smile. In his lap, Pikachu smacked his tiny yellow paw against his head. Misty shot him a questioning look, before shrugging her shoulders and walking away again to go and help Delia with dinner.

Breathing a sigh of relief - that was a close one - Ash let his mind wander back to his visit back to the Kalos region. He'd chosen to return for the amazing shopping district in Coumarine City, where he had gone searching for the perfect ring for Misty.

* * *

 **3 months earlier**

Ash let out a loud and frustrated groan as he walked away from yet another jewellery store.

"Pi, Pikachu."

"I give up, Pikachu, this is the hardest thing I've ever had to do," Ash looked down and complained to his best friend. Suddenly, he was forced to look up as a eerily familar voice whispered in his ear:

"Well, that doesn't sound like the Ash Ketchum that I remember."

Ash jumped up and turned around to see who was whispering in his ear.

"B-Bonnie? Clemont? Wow, you both look... Umm, different," Ash laughed, unable to find the words he wanted to use to describe the changes in his two old friends - Clemont had grown another five or six inches and filled out into a large muscular frame, now sporting a shorter hair style to the one Ash remembered him having. Bonnie on the other hand, while still noticeably shorter than her older brother, had the exact opposite figure to him: she was slim and athletic, with her now long blonde hair pulled up into a high side ponytail.

"So do you, you grew up...fine," Bonnie winked at him, placing her hand on his arm and causing Ash to go bright red and stutter - he never expected _that_ from her.

"BONNIE! HOW MANY TIMES HAVE I TOLD YOU NOT TO DO THAT!" Clemont chastised his younger sibling. Bonnie just shrugged her shoulders and apologised to Ash.

"BONNIE! CLEMONT!"

Ash turned around with his friends as another familiar voice called out, just in time to see a mousy brunette-haired girl running towards them. She ran straight into Bonnie's now open arms, greeting the blonde with a gentle and tender kiss.

"Serena, we've met someone today," Bonnie informed, letting go of her partner and indicating Ash.

"OH MY GOD! ASH! HIYA!" Serena babbled excitedly.

"Hey there, Serena," Ash replied happily, pleased to see his old friend.

Ash, Clemont, Bonnie and Serena sat down at the first free table in the Pokemon Centre along with all of their Pokemon.

"So, Ash, what brings you all the way back out to Coumarine City?" Bonnie asked, as she fed Dedenne one of Serena's famous Poke Puffs.

"I'm back here looking for an engagement ring, and I know for a fact that there are few better places to shop than in Coumarine City," Ash informed them.

"OH MY GOD! YOU'RE GETTING ENGAGED? THAT IS SO AMAZING!" Bonnie exclaimed excitedly, reminding Ash of when he first knew her as a little girl.

"Congratulations, Ash," Clemont added, offering his hand to Ash. He took his friend's hand and shook it, accepting the congratulations with a trademark grin.

"Well, I will be proposing if I can ever find the perfect ring for her," Ash admitted, the grin disappearing as he sighed loudly.

"Well, what's this girl like?" Serena asked.

"It's Misty, she's amazing, she's smart, funny, kind and caring and one of the best gym leaders I've ever faced," Ash admitted, blushing quickly at how easily he could praise her.

"Well, why don't you look for something that means a lot to her and to you?"

"Huh? What do you mean, Serena?"

"You said she was a gym leader, right? Well, why not see if you can make a ring out of her gym's badge?"

"That's a fantastic idea, Serena! Thank you!"

* * *

"Hey, Ash! Are we doing anything tomorrow?" Misty called down from upstairs, where she was still on the phone to Brock.

"No, we're free tomorrow."

"So is Brock. Wanna head down to Pewter City?"

"Sure thing."

Misty picked the phone back up and relayed that Ash and herself were free tomorrow and would see him in the afternoon.

 **The next day.**

Misty awoke with a yawn, stretching her arms as she reached out, her eyes still shut. Expecting her hand to meet Ash's scruff of hair, she opened her eyes when all she grasped was air. She sat up and looked around his bedroom, thinking he might be on his laptop at his desk, but all she saw was Pikachu asleep at the foot of their bed.

She didn't have to wonder for too long where he had got to, as a few seconds later she could hear him coming back up the stairs. Her eyes lit up as he made his way back into their room, carrying a large tray of her favourite breakfast foods.

"Oh wow Ash, thank you, this looks delicious," Misty beamed as Ash placed the tray down on her lap. "Where's yours?"

"Oh, I ate earlier, I just thought I'd do something nice for you" Ash told her, swallowing the lump in his throat. Ash stared at her for a moment, admiring the way the pale morning sun bounced off her, lighting up her smile even more than usual and making the sparkle in her eyes dance.

"Misty...I... " Ash began to say - but he froze, his throat suddenly seizing

"Yeah, Ash?"

"Nothing" Ash sighed, his head dropping dejectedly.

Ash got off the bed and walked away back downstairs, leaving Misty alone to finish her breakfast, wondering what had gotten into him. Once she had finished she brought the tray back downstairs, and as she was making her way to the kitchen she overheard Ash talking with his mom.

"I know it's hard, darling, but you can do this. All you need to do is speak from your heart," Delia reassured her son.

"I know - but simply 'I love you' isn't really gonna cut it this time," Ash complained.

"Don't worry, when the time comes you'll know exactly what to say."

"Thanks, mom" Ash beamed. Misty cleared her throat and stepped into sight.

"Hey, Ash - thanks for breakfast, it was amazing."

"No problem - here, let me grab that for you," Ash replied, getting up and taking the now empty plates and tray from her. After they were done tidying up in the kitchen, Ash and Misty decided to shower and go to see Professor Oak before heading off to Pewter City.

Ash knocked on Professor Oak's laboratory door and waited for him to answer.

"Good morning Ash, Misty," Professor Oak greeted the pair warmly as he opened the door to them. Ash and Misty returned the greeting and stepped inside; as soon as they did, Ash was charged down and tackled to the floor by his Muk.

"How are you, Professor?" Misty asked politely .

"I'm very well thank you and how are you both?"

"We're good, thanks."

"So what can I do for you two?"

"I was wondering if I could take Talonflame back, as we're going to Pewter City to see Brock and we thought it'd be easier to fly," Ash explained.

"Of course, let me just go and grab his Pokeball for you."

While Professor Oak was out of the room, Ash quickly put his arm around Misty's waist and pulled her closer to him.

"Misty, I love you" Ash whispered to her.

"I love you too," she whispered back, smiling as her cheeks grew ever so slightly pinker.

"Here you go, Ash." Professor Oak handed Ash the Pokeball he was holding as he re-entered the room.

"Thanks, Professor. We'll come back soon and have a proper catch up"

"Sure thing, Ash. Misty, take care of him"

"I will, Professor," Misty grinned.

A few hours later Ash and Misty slid off of Talonflame's back outside of Brock's Pewter City gym. Ash ran a quick hand through his Pokémon's feathers, thanking him for being so good.

"Talonflame, thank you, have a good rest. You've earned it". Ash put the Pokeball back into his pocket, slipped his hand into Misty's and walked into the gym.

"HEY BROCK!" Ash called out as they entered the gym. He was immediately shushed by someone stood right by the entrance and Ash could see why - they'd walked in on Brock while he was battling a trainer, a young blonde girl using a Whiscash against Brock's trusted Onix.

"Finn! Dodge it's Tackle and use Rock Slide followed by Waterfall!" Austyn called out to her Whiscash. It obeyed her instructions, dodging Onix's Tackle before unleashing a Rock Slide and Waterfall in quick succession. The speed of the moves were super effective and Austyn watched as Onix collapsed and fainted.

"The winner of the round and the match is the trainer from Hullumberside, Austyn!" The referee announced loudly. Brock walked over and shook her hand and handed over his gym's badge, congratulating her on a well fought battle. A tall brown haired boy ran over to Austyn and fist bumped her.

"Congrats, Austyn - level with me now," he grinned with a cheeky wink, pleased for his friend.

"Thanks, Grant, one step closer to going ahead of you," she replied and after mentioning needing to go to the Pokemon Centre, the two friends left the gym, sharing a joke.

Brock turned his back on the departing pair and his attention to his two old friends still stood at the edge of the battle arena.

"Hey, Misty, Ash."

"Hiya, Brock," Misty replied

"Hey, Brocko," Ash greeted his old friend, grabbing his hand in their old handshake. Brock led them to the back where he'd a small house built ajoining his gym, and in the kitchen they found Suzie cooking something that smelled absolutely delicious. She and Brock truly were made for each other, Ash thought to himself.

After he and Misty greeted Suzie, the four of them all sat down with drinks and began to catch up on what they'd all missed in each others lives. Suzie informed Ash and Misty that she and Brock were planning on moving to the Alola region.

"Oh wow, I've heard Alola is so beautiful," Misty exclaimed excitedly.

"I'm so happy for you both," Ash added. "Hey, Brock, can I quickly speak to you in private?"

"Uh, sure thing, Ash." Brock stood up and walked out of the kitchen, quickly followed by Ash.

Brock and Ash sat down in the living room, Ash shutting the door behind them, making sure that they wouldn't be heard.

"Brock, seriously, that was amazing news, congratulations," Ash repeated.

"Thanks, Ash - that means a lot, it really does" Brock replied. "So what did you wanna talk about?"

"I...I'm gonna ask Misty to marry me" Ash told him, and Brock's smile grew even wider at this news.

"Well, it's about time!" He laughed.

"Heh, yeah...The only thing is...I have no idea how to ask her or what to do for it." Ash admitted. Brock thought for a moment before shifting a little closer to Ash, close enough to whisper in his ear.

"Okay, here's what you do..." Brock began to whisper.

* * *

 **One week later**.

"A walk on Mt Moon? Why - what did you do?"

"Nothing!" Ash should have known Misty would be suspicious if he followed any of Brock's advice - it had been his least crazy suggestion (of course he wasn't going to cover their bed with roses, those things _hurt_!). "I just thought it might be nice to spend some time together." In an attempt to sound more convincing, he added, "And, okay, I guess there might be some pretty cool Pokemon to catch there too."

"Now _that_ sounds more like the Ash I know." But she'd smiled as she'd grabbed his hand, and she hadn't let go the whole time they'd been walking, through the tall grass at the base and up the mountainside, looming large over Pewter City, which they could see in the distance, bathed in a warm orange glow from the setting sun. The occasional Paras skittered across their path, but for once, Misty didn't even seem to care about the bugs.

"I guess you're right - this place does look beautiful tonight," she commented, as they paused for a break to take in the view. "I missed this, you know - it's been so long since I saw anything but the inside of the gym all day."

"Yeah," Ash agreed, stealing a glance at her profile - the way the sunlight shone on her face, the soft smile playing on her lips and the dreamy, faraway look in her eyes as she gazed out over the city - he couldn't resist adding: "But not as beautiful as you."

"Huh?" Misty turned to look at him, a slight blush colouring her cheeks even as she rolled her eyes with a laugh. "Ash, it's okay - you know you don't have to try and be romantic for me."

"I'm not just _trying_ to be romantic," he protested, not sure whether to be offended that his girlfriend didn't think he could be romantic on his own - it was hard to be, when he knew she was kinda right. "I really mean it!"

"Okay. Well, thanks." She squeezed his hand, her smile growing as they leaned in closer together. "You're not looking so bad yourself."

"Ow!" Their moment was interrupted as Ash felt a sudden sharp tug on his hair - okay, Pikachu, thanks for the reminder. He was so used to the weight on his shoulder after all these years, he'd almost forgotten the Pokemon was there as Misty shot him a puzzled look. He smiled innocently, taking a deep breath. "Actually, there's something I've been meaning to ask you..."

Just at that moment, an ear-splitting shriek pierced the air. They both jumped around just in time to see a whole flock of Zubat flying towards them - one huge flapping, squeaking purple cloud that looked like it was going to engulf them at any minute.

"They're in my hair!" Misty shrieked, covering her head with both hands.

"Quick - in here!" Still holding her hand, Ash ran for the nearest cave entrance, pulling both of them into the darkness. They finally stopped to draw breath when he was sure they were safe, and far enough inside to hear the flock of Zubat fly by as their cries faded out into the night.

"Wow," Ash said, leaning against the cave wall to catch his breath. "I wonder if something spooked them?"

"I don't know." He could feel Misty beside him, but it was so dark that he could only make out the tip of her ponytail and the faint curve of her nose in the shadows. "But it's really dark in here. Where did we come in?"

"Uh..." Ash looked around for a sign of light, or anything that might lead them back outside, but he couldn't see where they'd come from. But how hard could it be, right? They hadn't run _that_ far.

"Don't worry about it," he told her confidently - the last thing he wanted to do was mess up their time together already. "I'll get us out of here."

"Ash, would you just give up and admit it already? We're _lost_!"

"We're not lost!" Ash insisted, despite the fact they'd been wandering through the dark for...he wasn't sure how long, and only seemed to wind up back where they started. "I just...haven't figured out exactly where we are yet."

Misty let out a long, frustrated groan - he couldn't see her face, but he could picture her expression. "Tell me you at least brought a map?"

"I don't need a map! I've been here tons of times!"

"Yeah, like ten years ago!"

"I have a pretty good memory..."

"You have a _terrible_ memory!"

"Well, if you're so smart why don't _you_ get us out of..." Something wasn't right, Ash realised; he was missing something. Instinctively, he reached back for his shoulder, and grabbing at empty space, his heart sank. "Pikachu?"

"Don't try to change the subject -"

"No, Misty - I mean Pikachu's gone!"

"What?" Immediately, the anger in her voice was replaced by concern. "Maybe he ran away somewhere when those Zubat came?"

It really wasn't like Pikachu to just run off without telling him, Ash thought - it had to be something really big.

"Pikachu!" he yelled.

"Pikachu?" Misty joined in.

" _Pikachu_!"

They tried calling a little while longer, looking around for any telltale sparks of electricity, but there was no sign of the Pokemon.

"Oh, man," Ash sighed, dragging his fingers through his hair in frustration. "Pikachu, where _are_ you?! This really isn't how tonight was supposed to go..."

"Hey, it's okay." Misty's voice was softer, soothing, as he felt her lay a reassuring hand on his shoulder. "We'll find Pikachu - he must be in here somewhere."

"It's not just that..." Ash could feel the pressure of the last few days building up inside him, like a dam about to burst. "I really wanted to do something nice for you. I know I'm not always the greatest boyfriend, and maybe I'm more interested in Pokemon battles than romantic dinners or whatever. But I - I love you, Misty. I always have, even when I was a dumb kid. You're so smart, and beautiful, and fun, and great with your Pokemon, and you've always been there for me. I just didn't understand it back then." Ash took a breath - now he'd started he couldn't seem to stop, and he had to admit it was a relief to hear all the feelings he'd never quite been able to express pouring out. It was easier, somehow, with both their faces hidden in the shadows. "I thought winning the Kalos league would be all I ever needed - and sure, it was awesome. But I realise now - I could win every battle in the world, but none of it means anything, if - if I can't be with you."

"Ash..." Misty sounded - happy? Surprised? He still couldn't see, until there was a sudden flash of light, just illuminating her finger as it pointed to the corner of the cave. "Look over there."

"Huh?" Ash looked, and sure enough, there was a mysterious blue light, growing brighter as it cast an eerie glow throughout the cave. Then it began to separate into several smaller lights, moving around each other as a familiar, small, pink Pokemon hovered into view.

"Clefairy, Clefairy, Clefairy..."

Soft at first, the chanting soon filled the room as more and more Clefairy appeared, seemingly from nowhere and all holding their arms aloft as they glowed with magical energy.

"Uh - maybe we should..." Ash started to tug Misty away - from experience he was pretty sure they were preparing a Metronome, and that usually ended with someone getting blasted out of the room. But she held on to him stubbornly, transfixed as the Clefairy began to jump and dance around each other in some kind of pattern, their tiny hands all twinkling like stars as they continued singing.

"What are they...?" Ash's heart jumped as the Clefairy all stopped at once, turning to face them as another, much more familiar figure made its way forward, standing in the middle of the circle. "Pikachu!"

"Oh, Ash...it's _beautiful_." Finally, the combined light was bright enough to see Misty's face - lit up with pure joy and amazement, her eyes shining with wonder and what might even have been tears that she would probably deny later as she turned to him. "Did you - did you *plan* this all along?"

"I...uh..." Ash stared helplessly ahead at the scene in front of them - the Clefairy all looking at them expectantly as the realisation hit him - they'd come together to form a perfect heart shape, illuminated spectacularly by their magic. And at the centre -

"I guess you could say I had a little help from my friends," he said, grinning as he shot Pikachu a wink. His best friend smiled proudly back with a nod of approval, and Ash knew - it was time. It was now or never, and he'd never get a better moment than this.

"So I guess - what I've been _trying_ to say..." He dropped to one knee, wincing slightly as he hit the rough ground and fumbled for the ring he knew was in his other pocket. His heart was pounding like a Buneary on a bouncy bed as he extended the delicate box out to her, arm shaking slightly. "Misty, will you..."

Misty's eyes began to fill with tears at the sight of her boyfriend on one knee, holding a ring out - and not just any ring. He'd taken the Cerulean City gym badge and made it into a gorgeous ring. Ash was waiting with bated breath for what seemed like forever when finally he saw Misty open her mouth to reply.

"Ash...I'm pregnant." Misty replied.

She didn't know why she had just blurted it out like that - she had been waiting to tell him for weeks now, but didn't know how to bring it up. A look of surprise crossed Ash's face as his jaw dropped while Misty turned an alarming shade of red in horror when she realised that she had interrupted Ash while he was in the middle of proposing to her.

"...marry me?" he finally finished, totally dumbstruck.

"Yes, Ash, I will." She nodded, those tears now running down her cheeks, touching the corners of her mouth where she was smiling widely.

"All _right_!" Ash realised that it sounded as if he'd just caught a Pokemon, but Misty didn't seem to mind as she flung her arms around his neck and pulled him into a brief but passionate kiss.

"Pika pi!" They both jumped, and then started to laugh as Pikachu jumped up, somehow wriggling into the tiny space between them, seemingly not wanting to be left out. Misty laughed, reaching up to pet the Pokemon as he climbed up onto Ash's shoulder, and Ash couldn't believe how lucky he was. His Pokemon, his soon-to-be wife...and their baby. It felt like the start of a whole new journey.

It might have been the hardest question Ash had ever had to ask, but he couldn't have dreamed of a better answer.


End file.
